Water → 5-Methoxy-2-methylpyridine

HRID 273322Notes

Reaction equation

HRID 273322 reaction equation
CC(C)([O-])C.[K+].C[C:8]1(O)C=C[CH:11]=[N:10][CH2:9]1.CI.O.[CH2:18]1[CH2:22][O:21][CH2:20][CH2:19]1>>[CH3:20][O:21][C:22]1[CH:18]=[CH:19][C:9]([CH3:8])=[N:10][CH:11]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 691961363-Methyl-pyridin-3-ol

Product 1

HCID 133587775-Methoxy-2-methylpyridineYield 85%

Procedure

Potassium tert-butoxide (5.4 g, 48 mmol) was added to 3-methyl-pyridin-3-ol (5 g, 45.87 mmol) in THF (200 mL) at 0° C. The mixture was stirred at room temperature for 30 min. MeI (3.2 mL, 48 mmol) was added dropwise at 0° C. and stirring was continued at room temperature for 8 h. Water was added and the mixture was evaporated to half its volume and extracted with EtOAc. The organic layer was washed with brine and water, dried over anhydrous MgSO4, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography to give 5-methoxy-2-methyl-pyridine (4.8 g, 85%).

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for 8 h
  3. customthe mixture was evaporated to half its volume
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine and water
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a90c7cf25e0b49568eb4df56950bc39f
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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